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Classic Western songs about regret. Recommended popular tracks.

Here’s a list of classic Western songs about “regret.”

The genres vary—love, friendship, and regrets about the past.

As is often the case with Western music, the lyrics in each track feel disarmingly straightforward, almost awkwardly sincere.

There are some lesser-known hidden gems too, so don’t miss them.

Classic Western songs about regret: recommended popular tracks (41–50)

After The Love Has GoneEarth, Wind & Fire

Earth, Wind & Fire – After The Love Has Gone (Audio)
After The Love Has GoneEarth, Wind & Fire

It’s a wonderful song with depth and breadth.

As the title suggests, the lyrics deal with the pain, emptiness, and sadness that follow after love is gone.

This piece was included on the 1979 album Apocalypse.

The songwriting involved David Foster, Jay Graydon, and Bill Champlin, who were still relatively unknown at the time.

Classic Western songs about regret. Recommended popular tracks (51–60)

Careless WhisperGeorge Michael

George Michael – Careless Whisper (Official Video)
Careless Whisper George Michael

These are lyrics about someone who cheated but doesn’t want to give up on his girlfriend.

In romantic relationships, it’s common that even if the one who cheated regrets it, the person who was betrayed finds it very hard to forgive.

The content of the lyrics is unfortunate, but the song itself is wonderful.

After the FallJourney

Journey – After the Fall (Official HD Video)
After the FallJourney

A single released in 1983 by the American rock band Journey.

It’s a crisp and powerful rock ballad characteristic of Journey.

It was included on the album Frontiers, released the same year.

Although the sound comes across as energetic, the lyrics are quite serious, centered on the theme of “love fading away.”

The One That Got AwayKaty Perry

Katy Perry – The One That Got Away (Official Music Video)
The One That Got AwayKaty Perry

Rather than a heartbreak song, it’s closer to a memory song—or even a regret song.

The lyrics capture a very teenage vibe, about cutting loose and doing reckless things.

It’s poppy and easy to listen to, with an addictive hook that makes you want to sing it at karaoke.

The music video, which builds to a shocking ending, is a must-see.

PayphoneMaroon 5

Maroon 5 – Payphone ft. Wiz Khalifa (Lyric Video)
PayphoneMaroon 5

Even people who don’t listen to much Western music have probably heard the name Maroon 5.

In their hands—usually singing breezy songs about adult romance—even a breakup song becomes something refreshing and full of crisp coolness.

There’s nothing clingy about it even after being dumped; it’s truly refreshing.

Bye Bye ByeNSYNC

*NSYNC – Bye Bye Bye (Official Video)
Bye Bye ByeNSYNC

For people who aren’t into ornate wording or metaphors, this kind of breakup song is recommended.

Even though it’s a breakup song, it’s a track with a lively, upbeat parting vibe.

It makes you feel like maybe you need to be a little short on self-reflection to get through the pain of heartbreak.

This irresistibly pop song, just under four minutes long, is guaranteed to be one you’ll want to listen to over and over.

Let Her GoPassenger

Passenger | Let Her Go (Official Video)
Let Her GoPassenger

After we broke up and I lost them, I realized how I felt about that person and how important they were to me, and I regretted it deeply.

It’s a song filled with so much sadness and remorse that the tears start to flow naturally.

I think many people can relate to this song.